4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-2,4-dideoxy-D-gluco-oct-1-ethoxycarbonyl-2-Z-enitol | 214771-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-2,4-dideoxy-D-gluco-oct-1-ethoxycarbonyl-2-Z-enitol
• 英文别名: ethyl (2Z)-2-[(3R,4R,5S,6R)-3-acetamido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ylidene]acetate
• CAS: 214771-18-3
• 化学式: C₃₃H₃₇NO₇
• 分子量: 559.659
• InChiKey: SBRKDKKTCCQZQH-RPRADNPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-2,4-dideoxy-D-gluco-oct-1-ethoxycarbonyl-2-Z-enitol 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Stereocontrolled synthesis of β-C-glycosides and amino β-C-glycosides by Wittig olefination of perbenzylated glyconolactones derivatives

  摘要：

  Wittig olefination of perbenzylated glyconolactones afforded stereoselectively the Z-C-glycosylidenes which were transformed to the corresponding beta-C-glycosides and amino beta-C glycosides by hydrogenation followed by acetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01627-x
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-2,4-dideoxy-D-gluco-oct-1-ethoxycarbonyl-2-Z-enitol
  参考文献：
  名称：

  Stereocontrolled synthesis of β-C-glycosides and amino β-C-glycosides by Wittig olefination of perbenzylated glyconolactones derivatives

  摘要：

  Wittig olefination of perbenzylated glyconolactones afforded stereoselectively the Z-C-glycosylidenes which were transformed to the corresponding beta-C-glycosides and amino beta-C glycosides by hydrogenation followed by acetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01627-x

文献信息

• Alkylidenation of Sugar Lactones and Further Transformation to<i>C</i>-Glycosides
  作者：Juan Xie、Adeline Molina、Stanislas Czernecki

  DOI：10.1080/07328309908544013

  日期：1999.1

  The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar delta-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated beta-C-glycosides and amino beta-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino beta-C-glycosides. Other transformation of the enol ether function is also reported.
• Stereocontrolled synthesis of β-C-glycosides and amino β-C-glycosides by Wittig olefination of perbenzylated glyconolactones derivatives
  作者：Adeline Molina、Stanislas Czernecki、Juan Xie

  DOI：10.1016/s0040-4039(98)01627-x

  日期：1998.10

  Wittig olefination of perbenzylated glyconolactones afforded stereoselectively the Z-C-glycosylidenes which were transformed to the corresponding beta-C-glycosides and amino beta-C glycosides by hydrogenation followed by acetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.